Acetic Acid → 3,4-Dihydroxy-5-methoxy-3H-isobenzofuran-1-one

HRID 2268869Notes

Reaction equation

HRID 2268869 reaction equation
C([O:8][C:9]1[C:10]([CH:24]=[O:25])=[C:11]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:12](N(CC)CC)=[O:13])C1C=CC=CC=1.C(O)(=[O:28])C>Cl>[OH:28][CH:24]1[C:10]2[C:11](=[CH:19][CH:20]=[C:21]([O:22][CH3:23])[C:9]=2[OH:8])[C:12](=[O:13])[O:25]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 185047883-benzyloxy-N,N-diethyl-2-formyl-4-methoxy-benzamide

Product 1

HCID 185047873,4-Dihydroxy-5-methoxy-3H-isobenzofuran-1-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3-benzyloxy-N,N-diethyl-2-formyl-4-methoxy-benzamide (11.6 g, 34 mmoles), prepared as described in example 56, in 10% HCl (80 ml) and acetic acid (80 ml) was refluxed for 18 hours. The solvents were evaporated and the crude taken up in toluene. The solid was washed with ethyl ether and brought to dryness to give 6.66 g of the title compound (quantitative yield) which was used as such in the subsequent step.

Workup

  1. customThe solvents were evaporated
  2. washThe solid was washed with ethyl ether

Sources & evidence

ORD record
ord-98c30832322e464ba9c794e5fc5a9dd4
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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